Phosphate → (5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219055Notes

Reaction equation

HRID 219055 reaction equation
[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CS(O[CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:35][C@@H:34]([C:36]2[CH:47]=[CH:46][C:39]3[O:40][C:41]([CH3:45])([CH3:44])[O:42][CH2:43][C:38]=3[CH:37]=2)[O:33][C:32]1=[O:48])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[CH2:13][O:14][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]2[CH2:35][C@@H:34]([C:36]3[CH:47]=[CH:46][C:39]4[O:40][C:41]([CH3:44])([CH3:45])[O:42][CH2:43][C:38]=4[CH:37]=3)[O:33][C:32]2=[O:48])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 468322282-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonateHCID 66347770[3-(Cyclopentylsulfanyl)phenyl]methanol

Product 1

HCID 66845210(5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of [3-(cyclopentylthio)phenyl]methanol (270 mg) in dry DMF (10 ml) under nitrogen was treated with sodium hydride (60% dispersion on mineral oil, 57 mg) and the mixture stirred for 1 h. 2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate (0.4 g) in dry DMF (2 ml) was then added and the mixture stirred for 18 h. Phosphate buffer solution (pH6.5) was added and the mixture extracted with ethyl acetate. The combined extracts were washed with water and dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with 10% to 20% ethyl acetate-cyclohexane to give the title compound (0.23 g). LCMS RT=4.08 min.

Workup

  1. stirringthe mixture stirred for 18 h
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with 10% to 20% ethyl acetate-cyclohexane

Sources & evidence

ORD record
ord-abab926273c3438bb0018a9521d08837
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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